Thanks for all the support guys! I really appreciated your votes and comments! ^_^ sorry this one is a little bit longer ;)

After our first night together I honestly couldn’t stop thinking about him. I’d started babysitting for him more often, at least three times a week and he’d come back from work just a little bit earlier than usual. I always made sure I had the girls down for bed leaving us more free time to play around. One night we sat and talked about our fantasies, things we wanted to try that either hadn’t worked out correctly the first time or something we’d never done. He told me he wanted to bring one of my fantasies to life like I did for him. So I told him that I’d been curious about orgasming from anal and about the poor attempts I had in the past. I could never get there with another person. Whether it be because I just couldn’t relax enough or if it was because I felt like the other person was in a rush. He asked if I used plugs and I told him I had a set but I don’t use them often with anyone, mostly by myself. I think this piqued his curiosity which I was hoping it might because he became determined to make sure my attempt with him would be successful.

We planned for a weekend where the girls would be gone with their mother, giving us all the alone time to focus on each other. I brought over my 3 satin little pouches that the plugs came in and some lube. Mr. Owens led me to his bedroom which we had never been able to be in together for fear of his daughters waking up, so we always played downstairs. His room was big and the bed was large. It felt comfortable with the dim lighting from the nightstand lamps. Mr. Owens instructed me to get undressed and make myself comfortable. He left the room and returned with two glasses and a bottle of Reisling (I told him in the past it was my favorite). He poured my glass and told me to take my time with it, he got down on his knees by my feet and massaged my legs, ankles and calves. I sipped the wine slowly, letting the warmth wash over me and gently pull me down. As Mr. Owens hands worked up my thighs my heels arched and toes flexed naturally. He attentively kissed each of my toes and playfully nipped at them. Noticing my glass almost empty it was refilled and he then positioned himself behind me. Combing my hair to one side and lightly tracing my collarbone with his hand and massaging the nape of my neck with his thumb. I felt like a treasured doll in his possession. Not one inch of me went unnoticed.

The wine encouraged me to be at ease and I didn’t fight the passionate feelings rising inside me. I was brought to lay down on my stomach and to spread my legs only slightly. A light breeze passing through my legs and over my bald pussy caused me to shudder a bit but Mr. Owens warm hands gliding over my back felt nice and pleasant. I was then told to keep my eyes closed and focus only on what I could feel. Mr. Owens then left the bed and rummaged around my bag for the plugs and the lube. I didn’t see which of the three sizes he pulled out first but I assumed it would be the middle sized one, not too small, not too big. I told him that’s the one I usually went for when I was by myself. He spread my cheeks and let the lube slide down my hole and past my slit. He used the cold metal plug to spread the excess around and play with my clit. My body had become so warm that with the cold metal brushing against me I couldn’t stop myself from grinding back against it. The lube had made everything so slippery it was so easy to press my throbbing clit into the cold metal. Mr. Owens would slide the plug over the puffy lips of my pussy and rock the plug back and forth over my asshole, letting me feel the change in shape of the plug from tip to tail.

I patiently waited for that moment when I’d feel the plug push into me. When I’d feel the prick of it’s dull point spreading my ass and forcing the tight hole open. Mr. Owens would press and wait for me to relax before he’d start again. Feeling it slide in so slow it always feels like the plugs are so much bigger than they actually are. I believe it was about half way in before I started pushing my ass up to let Mr. Owens know I was ready for the rest. When it finally popped all the way in side my ass i immediately clenched around it. “It’s all the way in now baby, how does it feel?” Mr. Owens asked while caressing my bare ass and slipping a finger inside to massage the plug from the inside. I squirmed with his fingers inside me, he teased me like that for awhile. Thumb flicking against my clit while his fingers continued to play with my pussy. “Why didn’t you tell me plugs would make you this wet ?” He pulled his fingers out to show me the glistening strings of grool on his middle and ring finger. He pulled me on top of him, letting me straddle his cock before I guided it inside. When his thick cock slid in the plug pressing back against him made me feel even tighter than before. I didn't feel like they could both fit. I squirmed on Mr. Owens cock till it was nestled right behind my lower abdomen, that’s where I felt the most pressure. He guided me up and down his dick gently, helping me lift my hips as I rode him. We started out slow, building momentum each time he lifted me up. His dick sliding past the plug inside of me caused him to press a little more firmly against my g-spot and it felt absolutely amazing. It was hard to keep myself from bouncing too quickly but him stroking me so slowly caused me to cream all over his strong cock, it was heaven.

Mr. Owens brought me to lean forward so he could tug at the plug in my ass. Every time he’d tug a little bit and I’d whine and buck on his dick ridiculously. I really couldn’t help it, the sensation was driving me insane. I’d lost my inhibitions at this point and was completely in the moment. I begged him to shove his cock in my ass, “Daddy I want the real thing now, please give me the real thing now!” He finally removed the plug and pressed the head of his cock against my ass. The size difference really startled me and he encouraged me to relax and guide it in myself so that it be easier. He added more lube and while still on top of him I raised my hips and felt his thick meaty head begin to press into me. I focused on just managing to get the head in and then working the rest of him in gradually. I slowly pressed back against him and took the head of his cock inside me and pressed back again for more. I felt allll of him sliding past my tight hole that felt thoroughly stretched by now. I felt myself becoming anxious and hungrily pushed the rest of him in. I let out a yelp when I reached the base of his cock but I was so happy to feel cock so deep in my ass. A plug could never reach that far and honestly I was in bliss. I tried to ride him like I did before but it was too difficult so Mr. Owens rocked me back and forth so I could feel his dick moving inside my ass. I eventually could move my hips on my own and he was able to thrust a little against me. I leaned back on my arms and aggressively rocked my body against his. Even mildly feeling his cock moving in out of me was driving me crazy. I desperately rubbed at my clit feeling my stomach turning into knots trying to hold back my orgasm. I pleaded for Mr. Owens to keep going, I just keep thinking about him filling my asshole with hot cum and then I fucking exploded. I squirted all over Mr. Owens chest and stomach. I trembled and shook when his dick started spurting his milky cum inside me. It felt so good when he came in my ass that I used the excess cum to toy with my clit some more. It was hard to stop but eventually I gave out and finally was able to rest. We both laid there together out of breath and I dozed off full of Mr. Owens cum.

I appreciate the read! ^_^ Thank you for your votes ;)